Reaktion #46489

Reaktionsgleichung

2-aminonicotinic acid

LiAlH4

THF

→

title compound

Ausbeute 87.3%

2-Amino-3-(hydroxymethyl)pyridine

Ausbeute 87.3%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAn ice-bath was applied
2. 2
   Sonstigethe temperature below 30° C
3. 3
   workup.ADDITIONAfter the addition
4. 4
   Temperaturthe reaction was heated
5. 5
   Temperaturat reflux for 16 hr
6. 6
   Sonstigecarefully quenched by sequential addition of H2O (120 mL), 15% NaOH in H2O (120 mL), and H2O (350 mL)
7. 7
   workup.STIRRINGThe resulting thick suspension was stirred for 1 hr
8. 8
   Filtrationwas filtered through a pad of Celite®
9. 9
   WaschenThe filter pad was rinsed with THF (1 L)
10. 10
    Einengenthe filtrate was concentrated to dryness

Vorschrift

Solid 2-aminonicotinic acid (199 g, 1.44 mole) was added in portions over 4 hr to 1.0 M LiAlH4 in THF (3 L, 3 mole) with stirring under Argon. An ice-bath was applied to control the temperature below 30° C. After the addition was complete, the reaction was heated at reflux for 16 hr, then was cooled to 0° C. and carefully quenched by sequential addition of H2O (120 mL), 15% NaOH in H2O (120 mL), and H2O (350 mL). The resulting thick suspension was stirred for 1 hr, then was filtered through a pad of Celite®. The filter pad was rinsed with THF (1 L), and the filtrate was concentrated to dryness to give the title compound (156 g, 87%) as a pale yellow waxy solid: MS (ES) m/e 125.1 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 7.84 (dd, 1 H), 7.37 (m, 1 H), 6.53 (dd, 1 H), 5.65 (br s, 2 H), 5.16 (t, 1 H), 4.34 (d, J=4.6 Hz, 2 H).

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